A History Of Donald Trump's Investigations, Debt And Bad Business : It's Been a Minute with Sam Sanders What's next for President Trump once he leaves the White House? And what's next for his business? And what's he being investigated for again? And by whom?

We take a step back and break it all down with Andrea Bernstein, co-host of the WNYC & ProPublica podcast Trump, Inc., about Trump's finances, his mounting debt and how, after decades of bad business, he has always managed to find a way out.
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Why Donald Trump Is The Houdini Of Bad Business

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Why Donald Trump Is The Houdini Of Bad Business

Why Donald Trump Is The Houdini Of Bad Business

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SEAN SPICER: Good morning. Thank you for being here. We're now nine days away from the inauguration of the next president and vice president of the United States. It's an opportunity to be here today to allow the president-elect to take your questions. After the president-elect...


I want to take you back to another time, before this year's presidential election, before the pandemic, before Donald Trump officially took office - January 11, 2017.


MIKE PENCE: ...To introduce to all of you my friend and the president-elect of the United States of America, Donald Trump.


PRESIDENT DONALD TRUMP: Thank you very much. It's very familiar territory - news conferences - because we used to give them...

SANDERS: On this day in 2017 at Trump Tower, Donald Trump stood in front of a row of American flags, and he talked about plans for his presidency. And he also denied any deals with Russia. And he addressed how he might separate business Trump from President Trump.


TRUMP: As a president, I could run the Trump Organization - great, great company - and I could run the company - the country. I'd do a very good job. But I don't want to do that. Now, all of these papers that you see here - yes, go ahead.

ANDREA BERNSTEIN: I remember one of the things at that press conference - I mean, you know, people might remember it. So much has happened since, but maybe they remember it because it was his first press conference as president-elect.

SANDERS: This is Andrea Bernstein.

BERNSTEIN: And he was standing in front of this table with all of these file folders and butterfly clips.


TRUMP: These papers are just some of the many documents that I've signed, turning over complete and total control to my son.

BERNSTEIN: And from all the evidence that we can see, those papers were blank.


BERNSTEIN: But at that press conference, when Trump said that he was not going to divest from his business, it sent a signal around the world that he is somebody that could be bought or could attempt to be bought.


BERNSTEIN: And when you think about it, it's obvious. I mean, here's Trump. He came in as this incredibly transactional businessman who, you know, said quite clearly - stated himself that he made contributions and he gave money to people so that when he needed something from them, he would call them two years later, three years later, and when he called, they would do things for him. So he boasted about that.

So when he comes in to the White House and he says, I am going to continue to profit from my business as well, if you are a foreign despot, if you live in a country that is oligarchic, if you live in China or Russia or Saudi Arabia or any of these countries where the business model is, when you want something from the government, you pay off officials, what are you going to do but stay in Trump's hotels, but patronize his properties, but pay him money? And it set the template for what we have seen, which is this transactional presidency where people who pay the president or enhance his power or build up his brand get things, and people who don't get punished. And...


BERNSTEIN: ...We see this every single day. It's probably happening on Twitter right now while we're speaking.


SANDERS: You're listening to IT'S BEEN A MINUTE from NPR. I'm Sam Sanders. In this episode, we dig into the business of Donald Trump and what happens to all that business once he leaves the White House. The story of Trump's business interests over the last four years - it's complicated. He never really totally removed himself from those business interests once he won the presidency. And as he leaves office, Donald Trump is facing multiple investigations and lawsuits over those very business interests. He also has a lot of debt coming due very soon.

So how will Trump handle that without the protection of the presidency? If anyone has answers to that question, it is Andrea Bernstein. She is one of the co-hosts of the podcast "Trump, Inc." from WNYC and ProPublica. Coming up, she will break down just how much of a mess Trump is in come Inauguration Day, who is investigating what and how Trump has gotten away with so much for so long. That's coming up.


SANDERS: It can be hard to keep track of all the lawsuits and investigations that involve Donald Trump. Of course, there was the Mueller investigation, which didn't really change a whole lot for anybody. The Department of Justice made it fairly clear that it wasn't going to investigate a sitting president. But there are also these two ongoing investigations of Trump and his family businesses at the state level. One involves Manhattan District Attorney Cy Vance Jr. And another one involves New York State Attorney General Letitia James. Maybe the most striking of these two cases is the Vance case, which you might actually remember. It involves Trump's lawyer, Michael Cohen, and former adult film star Stormy Daniels, and how Michael Cohen paid Daniels a large sum of money to keep her quiet.

BERNSTEIN: So the campaign finance violations, the hush money payments, all of that.

SANDERS: Yeah, that case.

BERNSTEIN: Sometimes it's even hard to remember that happened, but it did.

SANDERS: That is all part of this investigation, which has grown a lot from looking into those hush money payments.

BERNSTEIN: So all of that was turned over to the Manhattan district attorney. And the Manhattan district attorney started to do what people do in white-collar criminal investigations, which is you ask for the paper trail. And you ask for the extensive paper trail because that's how white-collar crimes are cracked. It's like, you wouldn't try to do a homicide investigation without demanding fingerprints. You wouldn't do a white-collar investigation without asking for tax returns. So that's what Vance did. And when the DA of Manhattan, Cyrus Vance Jr., asked for Trump's tax returns from his accountants, Trump sued to stop that from happening.


BERNSTEIN: And he lost at the federal district court. And he lost at the appeals court. And he lost at the U.S. Supreme Court 7-2 and then went back to the district court with a new argument saying the subpoenas were overly broad and issued in bad faith.

SANDERS: Oh, wow.

BERNSTEIN: And he lost again. And he lost against at the Court of Appeals. And as we're recording this, the Supreme Court has not said whether it will hear the case. If it does not hear the case, then Vance can proceed with his investigation. And the presumption is that Vance has not been vigorously defending this on a lark, that he really has evidence of some kind of crime and strongly suspects something. So that could result in an indictment of the president or business associates or his family members or his business. All of that could happen. And we won't know - and I don't think Vance would actually know what he wants to do until he sees the evidence. But all of the...

SANDERS: Yeah. And then there's also another New York case, right? Tish James, the New York state AG, she's doing something, too, with Trump?

BERNSTEIN: Yes. So what she is doing is investigating whether Trump paid the proper New York state taxes.

SANDERS: Oh. Got you, got you, got you.

BERNSTEIN: And the reason that we even know about this is so interesting because, normally, this kind of thing would be kept well under wraps...


BERNSTEIN: ...Until such time as there was some kind of lawsuit filed or something public. But we know (laughter) about this because she subpoenaed Eric Trump...


BERNSTEIN: ...Who is running the family business. And Eric Trump said, OK, I'll come testify. And then a few days later, he canceled.

SANDERS: (Laughter).

BERNSTEIN: And he said, I'm not going to testify. And this is all politically motivated to embarrass my dad.


BERNSTEIN: And therefore, I will not be showing up. That's the point at which it became public because Tish James went to court - Tish James being the attorney general of New York - and said Eric Trump could not just duck his testimony. And a judge agreed and ordered Eric Trump to testify.

But in the legal papers, we learned a whole bunch of things about the scope of that investigation, that she is looking at possible tax evasion - in New York, in Chicago, in California - and a number of properties where Trump essentially overvalued properties when he was making contributions to charities but undervalued them on other forms - and also, in some places, apparently, did not declare forgiven loans as income, which you're supposed to do. So this is a civil case, but it is very much alive. And she has said, after the results were known, that she is continuing with that investigation.

SANDERS: And this is - so like, this Tish James case, is that at all related to The New York Times' story that found that Trump, one year, paid, like, only 750 bucks in taxes? Is that the same thing?

BERNSTEIN: So her investigation...


BERNSTEIN: Let me just say, The New York Times, to its great credit - and I hope they win another Pulitzer Prize for this - got Trump's tax returns, which is something that the district attorney of Manhattan couldn't do...


BERNSTEIN: ...And the AG of New York couldn't do and Congress couldn't do and Mueller never even tried to do. But The New York Times got them. However, their story didn't really come out until the end of September. And it's clear that Letitia James has been working on this case for some time. But the general trend (laughter) that The New York Times wrote about, where Trump would just overstate the value of his properties when he needed to make money and understate them when he needed to save money - for example, in taxes - it is the same theme that runs across all of this.


BERNSTEIN: You can't just make up numbers and put them on your tax returns. And there's evidence to suggest that that's what Trump did.

SANDERS: Wow. Wow. Back to Vance and his investigations. What do we think he could possibly suspect, like the scope of possibilities of what he is digging into?

BERNSTEIN: So (laughter) what people who have done white-collar criminal investigations have told me is that there's some tantalizing things, but they are not necessarily the most criminal things. For example, one of the things that came out in The New York Times' reporting was that Trump had spent tens of thousands of dollars - maybe upwards of $70,000 - of hairstyling and declared that a business tax deduction.

SANDERS: Oh, I saw that. And I was like, oh, not surprising.


SANDERS: I was like - you know? Makes sense.

BERNSTEIN: It is really the Trumpiest (ph) of the Trumpy (ph) things...


BERNSTEIN: ...That all of us have to live with his hairstyle and, according to Trump, pay for it, too.

SANDERS: (Laughter).

BERNSTEIN: But that kind of thing is not necessarily a criminal investigation.

SANDERS: Got you.

BERNSTEIN: So the more likely thing is some of the - our colleagues at ProPublica, for example, ferreted out that Trump's New York City property tax filings did not declare income - an income stream for various tenants. But filings for those same buildings at the same time - so an apples-to-apples comparison - with banks and securities filings suggested that the income streams were high. Well, why would Trump do that? - because he wanted to get the loan. He wanted to get the backing. He wanted to create confidence among lenders that these were going to be safe bets. So in this one example, this one apples-to-apples comparison, it looks like the numbers on the tax returns and the numbers on the bank loans did not match.

SANDERS: Got you.

BERNSTEIN: So that's the kind of thing that is a sort of outright tax fraud case that is not that complicated to prosecute. There's also questions of bank fraud, insurance fraud, you know? And (laughter) having spent the past four years deeply, deeply, you know, engrossed and reading over whatever records we can get about Trump's business and however we can report the information, all the evidence suggests that these things were not bugs. They were features of Trump's business model, that he has done this for decades.

SANDERS: Coming up, understanding Trump's businesses and how we have all, in a sense, paid for them.


SANDERS: You know, so we see that happening for four years. And now Trump is about to walk into all of those business interests that he was potentially edifying through his presidency the last four years. Can we just break down into big chunks what all of those business interests are right now? Like, I know there's the hotels. There's the resorts. There's the golf courses. There's the licensing stuff he does, with his name on buildings and things across the world. There's talk of a media empire. Like, how do you - as Trump walks back into his businesses, how do you classify the big chunks of what that empire is?

BERNSTEIN: Well, before I answer that, I just want to say that it's really clear that he is in business trouble. I mean, he went on this buying spree with golf courses about four years or so before he became president. This is a money-losing business, golf. Golf (laughter) is a sport that is aging out.


BERNSTEIN: It is losing money. And he sunk all of these resources into that. He runs hotels that are profitable but, you know, still are not doing great. And when you look at his...

SANDERS: And they've suffered since the pandemic and his presidency.

BERNSTEIN: Right, and have definitely suffered since the pandemic and have suffered since his presidency because a lot of them are located in blue states. So...


BERNSTEIN: ...His business is doing badly. And this is one of the things that was clear when The New York Times got ahold of his tax returns. We shouldn't be surprised by this. I mean, Trump has sort of been running a money-losing business almost from the beginning. I mean, he has just always lost money and...


BERNSTEIN: ...Gets away with it by making someone else pay. And he was in terrible shape in the early 2000s when Mark Burnett came to him and said, do you want to do "The Apprentice"? And that saved him. That really saved him...


BERNSTEIN: ...Because not only did he actually get a lot of cash from that but enabled him to market his brand around the world. But the biggest way the president has made money as president is from these two buildings that don't even bear his name - one's in San Francisco, one's in New York - where he gets a steady stream of commercial rent, including, we've learned - sometimes, people don't even have anything going on there, like the government of Qatar...

SANDERS: They just, like, own - they just rent the space to pay Trump?

BERNSTEIN: Yes. It's like - and it's not actually the...


BERNSTEIN: ...Government of Qatar, but it's a Qatari business that is backed by the government that has a rental in Trump's property in San Francisco. And Dan Alexander, who's a reporter for Forbes magazine, went there and - just empty. It was just like, you know, a shell. But Trump has managed to get a stream of money from that.

Now, you know, I think one of the things that's being bandied about a lot is that he's going to try to start some kind of media empire. He's on a tear now against Fox News. So that would seem to be the kind of prologue that we would expect knowing Trump. But, of course, he would need to get somebody to fund it. He certainly isn't going to get any bank loans. And (laughter) speaking of bank loans...


BERNSTEIN: ...He has a lot of money coming due. He has hundreds of millions of dollars coming due.

SANDERS: OK, this was my next question. Yeah, I didn't know this was the case. So I was prepping for this interview - he has a bunch of liabilities in his private business life, a bunch of loans and debts that are coming through. I've read reports that it's anywhere from, like, hundreds of millions of dollars that he will owe in loans in the next few years. What? How? Explain, please.

BERNSTEIN: (Laughter) Yeah, it's true.


BERNSTEIN: So you remember the golf courses. So Trump went on a bit of a lending spree, and he borrowed money for his golf courses. He borrowed money for his Washington, D.C., hotel. He borrowed money to pay off some other debts, most of it from the German bank Deutsche Bank.

What became clear when The New York Times got a look at his tax returns was so fascinating, and it was so Trumpian because he wanted to create a situation where he would reduce his tax liabilities. So you can do that if you personally guarantee part of your debt. So he did that. He personally guaranteed part of his debt. But that means that he personally has to pay it back.

SANDERS: That means he owes it.


SANDERS: Is there any indication that he can actually pay it back?

BERNSTEIN: Well, there is not an indication that he has that kind of store of cash. And the president doesn't have an apparent stream of cash coming in. So you have the situation where he has a financial incentive to hang on to the presidency - had and has - or has and had.

SANDERS: Wow. Yeah.

BERNSTEIN: Because he - I mean, what would you do if you were a bank and the president of the United States owed you hundreds of millions of dollars? Would you default on the president of the United States? Well, the incentives are not to do that because that person can control macro and microeconomic policy in a way that could affect your bank. And it's Trump, and Trump has shown that he's willing to be sort of petty and vindictive. So it put the banks in this incredibly awkward position had he been reelected because if they forgave his debt, it would be a huge gift to the president, unprecedented in size. And if they didn't, they would risk crossing him. So that was the situation that we faced.

But he still has to figure out how he's going to pay the debt. And, you know, one of the things he's done all his life is he gets someone else to pay his debt. So he borrows money, and he gets someone else to pay it. Now, someone else may be the bank has to pay their own debt. It might be a business associate. It might be the taxpayers in the way that he pays no taxes because he keeps losing money. So we all have paid for Donald Trump to continue this business model where he accrues debt and rolls it over and rolls it over and rolls it over.

SANDERS: And I don't even golf. I'm mad. I don't even golf.

BERNSTEIN: Right, right. Well, that is the thing about a tax deduction - is that you don't necessarily have the experience of any of these Trump properties. And yet, what is a tax deduction? It's your money that's funding that business.

SANDERS: Yeah, yeah. You know, there was a town hall this election season where Trump talked about the debt that he has and those loans. And he said it was small as a peanut. And he said that the way that he carries debt is reasonable and smart. Was he at all right in saying that?

BERNSTEIN: Yeah, no (laughter).


BERNSTEIN: Nobody that I've ever spoken to in banking or real estate thinks that this is anything like a normal business model. I mean, to be clear, real estate is an industry that is based on debt, but it is not based on not paying off your debt over and over and over again. And that was what Donald Trump has done. And he's sort of, you know, exalted in the fact that he's managed to pull the wool over people's eyes.

There's this incredible passage in "The Art Of The Deal" where he talks about - so his first - very first deal in Manhattan was at a hotel - is now called the Grand Hyatt. Then it was called the Commodore Hotel. And Donald Trump wants to buy the building, and he wants to get a huge tax break from the state. And he has to go through this incredibly complicated series of transactions in order to get this all to work. And at one point, the state officials say, do you have the financing? And he says, oh, yes, I have the financing. He doesn't have the financing. And the bank officials say, do you have the state approvals? And he says, oh, yes, I have the state approvals. And he doesn't have the state approvals. And then he goes and he files papers with the state agency that has to approve the deal that doesn't have the bank's signature. And no one notices that it was only his signature on the paper.


BERNSTEIN: And he was so excited about this ruse that he has pulled off that he boasts about it in his book. And that was his first big deal. And that has pretty much been the template for all of his deals.

SANDERS: Wow. Wow. You know, as - big-picture, has the last four years of Trump as president been good or bad for his businesses on net?

BERNSTEIN: Yeah, you know, it's such a complicated question to answer because in order to answer that, you have to be able to sort of know the counterfactual, which is what would've happened had he not been president, right? And already, from having run his presidential campaign, we know that there were certain businesses that were shying away from him. There was a big incident where Jose Andres, the noted chef, was like, I'm not working in your hotel in Washington, D.C., because of the things that you've said about Mexicans. And there was a lawsuit, predictably, by Trump.

SANDERS: Yeah, I remember that. Yeah.

BERNSTEIN: NBC severed ties. So there was a lot of things that were happening even prior to Trump's presidency as he became really vocal, particularly in his, you know, anti-immigrant rhetoric.

So what we do know is that he's been able to make, for example, his hotel in Washington the sort of center of lobbying activity. Everybody who's anybody understands that you have to go there and be seen to be a player in the Trump administration. And we've seen all kinds of examples of that.

He's also been able to make money by deciding at whim when he wants to go to one of his properties, in which case there's all kinds of government expenses that are triggered. There's Secret Service. There's staff money. There's money for the people who - the advanced people who have to go and set up this. So...

SANDERS: Yeah. I heard they charge for the golf cart usage of the Secret Service agents.

BERNSTEIN: The golf cart usage. They've charged for water at a Trump event.


BERNSTEIN: They've charged for a cottage at his Bedminster resort. I mean, The Washington Post has really done sort of terrific reporting on this.


BERNSTEIN: But he has been able to get an income stream from the federal government just by going there, and there's no one who can tell him not to.

SANDERS: Wow. Yeah.

BERNSTEIN: So he just decides when he wants to go, and all of this money goes into his businesses. So there's definitely people who are patronizing his properties that were not patronizing his properties before and that are doing it precisely because Donald Trump is the president. You know, the Saudi government at one point booked a block of 500 rooms at one of his hotels...

SANDERS: Wait; really? Wow. This is just (laughter)...

BERNSTEIN: ...Making it go from an unprofitable quarter to a profitable quarter.


BERNSTEIN: So it's (laughter) really hard to say, you know, sort of what would've happened.

SANDERS: Yeah, yeah.

BERNSTEIN: I mean, you know, the other thing about being president is that, you know, typically, the post-presidency period is quite lucrative, and it's unclear sort of where that is going. I mean, for example, he did not end up doing a licensing deal with China. He did not end up building a Trump Tower Moscow. Could those things be re-triggered now that he is going to be an ex-president? Maybe. Would they be more valuable in Moscow or in China? Maybe. So it's, I think, a really, really, really sort of difficult-to-answer and murky question. But one thing is clear. Trump was not a successful businessman, even though he played one on TV. And he still...

SANDERS: And he still does it.

BERNSTEIN: ...And he still wasn't.

SANDERS: (Laughter) Well, I'm even just thinking about the typical things that presidents do once they leave office. And even if he's very good at those things, I'm not sure they'll be enough. You know, he could go on the speaking circuit and get six-figure speaking fees. He could sign a seven-figure book deal or eight-figure book deal. It seems like that still wouldn't be enough to pay off all this debt he owes. Like, he'd have to do so well post-presidency to cover all this stuff that you're laying out for me.

BERNSTEIN: You know, I keep saying to myself, the chickens may finally be coming home to roost. However...

SANDERS: However (laughter).

BERNSTEIN: ...Having watched Donald Trump's business and, you know, paid attention to it and really gone deep and long ago into the family business records from the 1950s and looking at those things, every time, he manages to pull a Houdini.


BERNSTEIN: So I never would want to say that that is impossible because I think there've been plenty of times where it seemed like there was no way out for Donald Trump, and he found a way out.

SANDERS: Wow, wow. Last question for you. Sum up everything you've learned about Trump and how Trump Inc. works. Everything you've covered the last several years - sum it up in one sentence, the moral of this Trump business story or the throughline or the big lesson here.

BERNSTEIN: Boy, oh, boy (laughter). You know, I think the shortest way to say it would be, we pay, he wins.


SANDERS: Thanks again to Andrea Bernstein. She is the co-host of the WNYC and ProPublica podcast "Trump, Inc." Also, Andrea has a book. It's called "American Oligarchs: The Kushners, The Trumps, And The Marriage Of Money And Power."

All right, listeners, don't forget; this Friday, we are back with another episode. For that episode, we want to hear from you in our Best Things segment. Just tell me the best part of your week. Send that voice file to me via email to samsanders@npr.org - samsanders@npr.org. Also, listeners, if you like this show, even if you don't, please leave us a review on the podcasting app of your choice - maybe Apple Podcasts. Consider it. Also, tell a friend about the show.

OK, that's it for me. Till Friday, thank you for listening. Be good to yourselves. I'm Sam Sanders. We'll talk soon.


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